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Chemistry

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Also known as: 1255at22zj, Unii-1255at22zj, Vip152, Chembl4762845, Vip-152, Bay-1251152

Molecular Formula

C₁₉H₁₈F₂N₄O₂S

Molecular Weight

404.4 g/mol

InChI Key

YZCUMZWULWOUMD-NDEPHWFRSA-N

FDA UNII

1255AT22ZJ

Enitociclib is an inhibitor of cyclin-dependent kinase 9 (CDK9), the catalytic subunit of the RNA polymerase II (RNA Pol II) elongation factor positive transcription elongation factor b (PTEF- b; PTEFb), with potential antineoplastic activity. Upon administration, enitociclib binds to and blocks the phosphorylation and kinase activity of CDK9, thereby preventing PTEFb-mediated activation of RNA Pol II and leading to the inhibition of gene transcription of various anti-apoptotic proteins. This may cause cell cycle arrest and induce apoptosis, which may lead to a reduction in tumor cell proliferation. The protein complex PTEF-b, a heterodimer consisting of CDK9 and a regulatory cyclin subunit of the T family, is over-activated in various tumor cell types; it plays a key role in the regulation of Pol II-mediated transcription of anti-apoptotic proteins. Tumor cells are dependent on anti-apoptotic proteins for their survival.

1 2D Structure

Enitociclib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-[4-[(methylsulfonimidoyl)methyl]pyridin-2-yl]pyridin-2-amine

2.1.2 InChI

InChI=1S/C19H18F2N4O2S/c1-27-17-8-13(20)3-4-14(17)15-9-19(24-10-16(15)21)25-18-7-12(5-6-23-18)11-28(2,22)26/h3-10,22H,11H2,1-2H3,(H,23,24,25)/t28-/m0/s1

2.1.3 InChI Key

YZCUMZWULWOUMD-NDEPHWFRSA-N

2.1.4 Canonical SMILES

COC1=C(C=CC(=C1)F)C2=CC(=NC=C2F)NC3=NC=CC(=C3)CS(=N)(=O)C

2.1.5 Isomeric SMILES

COC1=C(C=CC(=C1)F)C2=CC(=NC=C2F)NC3=NC=CC(=C3)C[S@@](=N)(=O)C

2.2 Other Identifiers

2.2.1 UNII

1255AT22ZJ

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 1255at22zj

2. Unii-1255at22zj

3. Vip152

4. Chembl4762845

5. Vip-152

6. Bay-1251152

7. 1610408-97-3

8. 2-pyridinamine, 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-n-(4-(((s(s))-s-methylsulfonimidoyl)methyl)-2-pyridinyl)-

9. 2-pyridinamine, 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-n-[4-[[[s(s)]-s-methylsulfonimidoyl]methyl]-2-pyridinyl]-

10. Enitociclib [inn]

11. Enitociclib [usan]

12. Gtpl11686

13. Glxc-26844

14. Bdbm50556034

15. Bay 1251152

16. Csc(s)-[(2-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]amino}pyridin-4-yl)methyl](imino)(methyl)-l6-sulfanone

2.4 Create Date

2019-11-19

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₈F₂N₄O₂S
Molecular Weight	404.4 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	6
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	96.3
Heavy Atom Count	28
Formal Charge	0
Complexity	619
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1